Welcome to the Southernmost Point in the Continental US

Key West, with its vibrant streets and laid-back island vibe, offers an unforgettable experience with a mix of adventure, live music and local cuisine. This unique island at the end of the Florida Keys is perfect for those seeking a soulful fusion of culture, cuisine, and sights. Whether you're a history lover, a foodie, an adventurer at heart, or just like to have a good time, Key West is a perfect destination.

Day 1: Arriving in Key West

Whether you are driving, flying or taking the ferry to Key West, it does take a bit of time to travel all the way down here. While we only had to drive from Marathon on this visit, we got a late start, so our first destination was for brunch at Sunny Eggs. We found this to be a charming cafe that lived up to it's high online reviews. The cafe stands out with its mouthwatering pastries and French inspired dishes. Order a cocotte if you are feeling adventurous and want to try eggs in a French-style Dutch oven, but if not, the popular Palm Breakfast is a good choice too. We would recommend arriving earlier than we did to not miss out on the variety of fresh baked pastries.

Next we had to catch some live music at one of the many well-known establishments in Key West. The Green Parrot is a quintessential dive bar rich in history and character. A staple for both locals and visitors, it’s the embodiment of Key West’s lively spirit with its genuine dive atmosphere and laid back crowd. Whether you’re drawn in for a cheap drink or just to enjoy the company of local rooster friends, you’re in for an authentic slice of Key West life.

When the band at the Green Parrot goes on break, there is no shortage of other bars and restaurants to pop into, including General Horse Play, where patrons can participate in the thrill of a dice roll to determine drink prices if visiting during Happy Hour. This concept added an exciting twist to our visit. We tried two craft cocktails, the Unicorn Heart, which came with a strawberry covered in edible glitter, and the Spiced Banana Daquiri, which included a bruleed banana bite.

No visit to Key West is complete without a selfie at the Southernmost Point Buoy. This symbolic monument marks the southernmost tip of the continental United States and makes for a coveted photo op for tourists. While this is a free attraction, lines can get long and the sun can be intense, so come prepared to stand in the heat to get that perfect shot.

After listening to music, having some drinks and snapping a photo at the Southernmost Point, The Alamo is a great spot for dinner, as it offers a Happy Hour and drinks and food, as well as live music. Our favorite item by far was the tuna nachos.

To wind down on your first day in Key West, head to the serene shores of Fort Zachary Taylor State Park. The park blends history with natural beauty, offering plenty of spots to explore. Wander the fort or sink your toes in the sand as you await a breathtaking sunset. Tip: If you do want to experience both the fort and the beach, keep in mind the fort closes at 5 pm. 

Day 2: Off Shore Fishing & Key West's Authentic Key Lime Pie

We recommend starting your second day out on the water. We left early out of the marina with Reef Runner Charters. We had booked a 3/4 day off shore fishing excursion. Captain Edward and Captain Tom took us into the deep blue to fish for mahi. The day felt like a roller coaster in more ways than one, but ended on a high note. While there are a ton of options for fishing charters out of Key West we do recommend Reef Runner as Captain Edward grew up on Key West and his knowledge of fishing this area is what led to us catching plenty of fish. He was more than willing to share tips and tricks he has picked up over the years, as well as stories from growing up in the Keys.

Now if you aren't into fishing, but still want to get out on the water, you will have plenty of experiences to choose from like this morning snorkeling tour.

After hours on a boat in the Florida summer heat, you may need a drink, a place to cook your catch and a good slice of Key Lime Pie - you can find all three at the famous Blue Heaven. Known for its lush courtyard, roaming chickens, and the most authentic Key Lime Pie, it’s a must stop in our opinion. The Key Lime Pie was much different than what we expected, but we still recommend stopping by to see what makes this slice so special.

Day 3: Key West by Day & Night

If you want to experience historic Key West into the evening on your third day, you may want to start with some strong coffee on Duval Street. We chose Doing Work Coffee as they offer bourbon barrel aged coffee beans. This spot can be easy to miss as it is located inside the Wicked Lick ice cream shop.

Next you've got your pick of Key West's many famous attractions. We recommend visiting The Hemingway Home as this historic site offers a peek into the life and mind of one of America’s great authors. The grounds, famous for their six-toed cats and lush gardens, are equally alluring as the main house. Whether you’re there for the architectural beauty or the feline friends, the essence of Hemingway lingers in each room and pathway.

Tip: free parking can be very hard to come by in Key West, it is very common to get around via bicycles, scooters or golf carts. There are plenty of rental places to choose from but you can also take the Old Town Trolley or the Conch Train.

For lunch, Seaside Cafe offers a captivating combination of coastal views and creative dining options including its well-loved lobster pizza. This restaurant is located within the grounds of the Southernmost House, where you can actually book a room to stay on Key West, and we can tell you, the lobster pizza did not disappoint!

The #1 rated attraction in all of Key West is located only a block away from the Seaside Cafe, the Key West Butterfly and Nature Conservatory. We easily could have stayed here all afternoon watching the butterflies and birds. It was fun to try and stay as still as possible and wait for the butterflies to land on us.

While the butterfly conservatory is a well-known attraction, the Key West Garden Club is a bit off of the beaten path. It is located right next to Higgs Beach. This area is just as beautiful will less butterflies and tourists. While it is free, it does accept donations as the grounds are kept by volunteers.

For dinner Key West's Original Seafood Restaurant is a good choice. Half Shell Raw Bar is known for having one of the best Happy Hours on the island. Our favorite item was the Lobster Egg Roll. We'd love to go back and try a dish off of their regular menu.

When it's time to unwind for the evening stop in at Sloppy Joe’s, an iconic bar relishing in its historical charm and lively environment. This place has a raised stage and gets used every day by multiple music artists and bands. We enjoyed two different bands here on our visit and even though it was a Tuesday during the low season the place was packed!

Finally, no Key West journey is complete without an escape to Captain Tony’s Saloon. This establishment has a colorful history as well as long list of famous patrons. While this spot also hosts live music, the vibes are much different from Sloppy Joe's. You won't want to leave without trying your luck at tossing a quarter into the famous grouper.

Closing out Key West

We hope this itinerary gives you more than a few ideas of what to do and where to eat & drink during your next trip to Key West. If you really want to get a feel for all of the destinations identified within this guide, we'd recommend watching our Key West travel guide to help determine which spots are best for you. To see even more Florida Keys itineraries and travel guides be sure to follow us here on Plannin and Youtube.